Triethylamine → HCID 67384038, compound

HRID 1958326Notes

Reaction equation

HRID 1958326 reaction equation
CO[C:3]([C:5]1[C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=[CH:7][N:6]=1)=[O:4].[C:14]1([C:20]2[N:21]=[C:22]3[N:27]=[C:26]([NH2:28])[CH:25]=[CH:24][N:23]3[CH:29]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([N:32]([CH2:35][CH3:36])[CH2:33]C)C>ClCCl>[N:32]1([C:3]([C:5]2[N:6]=[CH:7][CH:8]=[CH:9][C:10]=2[C:11]([NH:28][C:26]2[CH:25]=[CH:24][N:23]3[CH:29]=[C:20]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:21]=[C:22]3[N:27]=2)=[O:12])=[O:4])[CH2:33][CH2:36][CH2:35]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13239660Methyl 3-(chlorocarbonyl)pyridine-2-carboxylateHCID 508783902-Phenylimidazo[1,2-A]pyrimidin-7-amine

Product 1

HCID 67384038HCID 67384038, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Chlorocarbonyl-pyridine-2-carboxylic acid methyl ester (620 mg, 3.1 mmol) was added slowly to a solution of 2-phenyl-imidazo[1,2-a]pyrimidin-7-ylamine (step 1, example 1, 470 mg, 2.2 mmol) and triethylamine (566 mg) in dichloromethane (7 ml), and the mixture was stirred overnight at RT. The mixture was diluted with additional dichloromethane, and washed with water. The combined organic layers were dried (Na2SO4), the solvent was evaporated, and the title compound (490 mg, 49%) was obtained from the residue by column chromatography (silica gel, dichloromethane:methanol=50:50-0:100). MS (m/e)=374.2 [M+H+].

Workup

  1. washwashed with water
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d7f558547b8f4f6ea7c9a4fb3de4e0bc
Source dataset
uspto-grants-2013_04
Patent number
US08410117B2

Reaction notes

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